EP0908486B1 - Wasserverdünnbare Harze, Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents

Wasserverdünnbare Harze, Verfahren zu ihrer Herstellung und ihre Verwendung Download PDF

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Publication number
EP0908486B1
EP0908486B1 EP98118725A EP98118725A EP0908486B1 EP 0908486 B1 EP0908486 B1 EP 0908486B1 EP 98118725 A EP98118725 A EP 98118725A EP 98118725 A EP98118725 A EP 98118725A EP 0908486 B1 EP0908486 B1 EP 0908486B1
Authority
EP
European Patent Office
Prior art keywords
acid
water
resins
carbon atoms
resins according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP98118725A
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German (de)
English (en)
French (fr)
Other versions
EP0908486A2 (de
EP0908486A3 (de
Inventor
Peter Dr. Tümmler
Gerald Dr. Hobisch
Hellmuth Dipl-Ing. Kasch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Allnex Austria GmbH
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Surface Specialties Austria GmbH
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Publication date
Application filed by Surface Specialties Austria GmbH filed Critical Surface Specialties Austria GmbH
Priority to AT98118725T priority Critical patent/ATE263798T1/de
Publication of EP0908486A2 publication Critical patent/EP0908486A2/de
Publication of EP0908486A3 publication Critical patent/EP0908486A3/de
Application granted granted Critical
Publication of EP0908486B1 publication Critical patent/EP0908486B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers

Definitions

  • the invention relates to pigment pastes as suitable, water-dilutable after neutralization resins obtainable by reaction of hard resins based on aldehydes or ketones with a binder-like, water-dilutable after neutralization polycarboxylic.
  • Hard resins based on aldehydes or ketones in technical language in simplified form usually as Aldehyde or ketone resins referred to, have long been known. These hard resins are due to their specific coating properties, such as light color, saponification and Yellowing resistance, good compatibility with other paint binders and very good solubility in polar organic solvents important raw materials for nitro lacquers and alkyd resin lacquers. Also in special fields of application, for example as a base resin for solvent-containing Universal pigment pastes, they have gained great practical importance in recent years.
  • the object of the present invention was to provide water-dilutable resins based on aldehyde or ketone resins, the usability of these resins as a binder component, and especially as pigment paste resin, for waterborne paints too without adversely affecting the properties of the underlying coating system.
  • the invention enables the production of general purpose, low-solvent pigment preparations.
  • aldehyde and ketone resins with specially selected ones binder-like, water-dilutable after neutralization polymers selected from Acrylate copolymers and polyesters having a high content of carboxyl groups, as well as with carboxyl-containing components by dimerization or oligomerization are accessible from unsaturated aliphatic carboxylic acids, at least partially condense, in this way good water-dilutable, as an aqueous dispersion Store-stable, novel paint binders are obtained.
  • Suitable Acid Group-Containing Polymers (Polycarboxyl Components) of the acrylate copolymer type are described, for example, in AT 396 244 B 1 ( ⁇ EP-A 0 496 079) and in AT 388 921 ( ⁇ EP-A 0 295 403).
  • the acid number is defined according to DIN 53 402 as the quotient of the mass m KOH of potassium hydroxide required to neutralize a sample to be investigated and the mass m B of this sample (mass of the solid in the sample in the case of solutions or dispersions); their usual unit is "mg / g".
  • Suitable components A are acid group-containing copolymers of olefinically unsaturated monomers having an acid number of the copolymer of from 30 to 240 mg / g.
  • Such copolymers are preferably prepared by carrying at least one of the olefinically unsaturated monomers used, namely Al, at least one acid group, preferably a carboxyl group.
  • One or more of these monomers A1 are polymerized together with one or more monomers A2, which are free of acid groups. It is also possible to change the composition of the monomer mixture during the polymerization. By a suitable choice of the type and amount of the monomers, the desired acid number can be easily adjusted.
  • Suitable ⁇ , ⁇ -unsaturated carboxylic acids are acrylic and methacrylic acid, crotonic and isocrotonic acid, vinylacetic acid, 3-propylacrylic acid and 2-octenoic acid.
  • Suitable monoalkyl esters of ⁇ , ⁇ -unsaturated dicarboxylic acids are monomethyl, monoethyl, monopropyl and monobutyl esters such as monomethyl maleate, Monäthylfumarat, Mesaconklamonobutylester and trans-3-Hexendiklamonopropylester. These acid group-containing monomers are preferably used in proportions by mass of from 10 to 33%, based on the mass of the monomer mixture.
  • the monomers A2 which are free from acid groups are selected from the alkyl esters of monobasic ⁇ , ⁇ -unsaturated aliphatic carboxylic acids having 3 to 7 carbon atoms in the acid component and 1 to 20, preferably 1 to 12 carbon atoms in the alkyl component; the dialkyl esters of ⁇ , ⁇ -unsaturated aliphatic dicarboxylic acids having 4 to 8 carbon atoms in the acid component and 1 to 20, preferably 1 to 12 carbon atoms in the alkyl component; the nitriles of said acids; the hydroxyalkyl esters of said monobasic ⁇ , ⁇ -unsaturated aliphatic carboxylic acids having from 3 to 7 carbon atoms in the acid component and from 2 to 20 carbon atoms in the hydroxyalkyl moiety, including oligo-oxyalkylene glycol monoesters having a number average degree of polymerization of from 2 to 50, their alkylene groups the ethylene and 1,2-propylene groups and mixtures
  • mono or polyunsaturated fatty acids having 14 to 30 carbon atoms or their esters with aliphatic alcohols having 1 to 20 carbon atoms in the alkyl group can also be used as further monomers A3 .
  • suitable monomers A3 are oleic acid, linoleic acid, linolenic acid, ricinensic acid and mixtures of such acids as safflower oil fatty acid, soybean oil fatty acid, linseed oil fatty acid, cottonseed oil fatty acid, sunflower oil fatty acid and tall oil fatty acid and esters thereof.
  • the mass fraction of these monomers A3 in the monomer mixture of A1, A2 and A3 is then 0 to 50%.
  • the polymerization of the monomer mixture is carried out by the known methods, preferably by free-radical polymerization.
  • initiators the known Peroxides, peracids and their derivatives, azo compounds and also as redox catalysts known pairs of oxidizing and reducing agents, also together with Salts of transition metals such as iron, cerium or manganese are used.
  • the Polymerization can be carried out in solution, emulsion or else in bulk.
  • a molar fraction of up to 10% of component A4 may be replaced by tri- or higher aliphatic linear, branched or cyclic alcohols having three to 20 carbon atoms.
  • a mole fraction of up to 10% of component A5 may be replaced by a tri- or polybasic aliphatic or aromatic carboxylic acid.
  • the polyesters can also be condensed with the concomitant use of mass fractions of up to 15% of hydroxycarboxylic acids A6 , each having at least one hydroxyl group and at least one carboxyl group.
  • alcohols A4 for example, preferably ethylene glycol, 1,2- and 1,3-propylene glycol, 1,4-butanediol, neopentyl glycol, 1,6-hexanediol, 1,2- and 1,4-dihydroxycyclohexane, 3,4-diethyl 3,4-hexanediol and 1,4-bis (hydroxymethyl) cyclohexane are used in each case individually or in a mixture. Particularly preferred are glycol, neopentyl glycol and 1,2-propylene glycol.
  • Adipic acid, succinic acid, sebacic acid, cyclohexanedicarboxylic acid, phthalic acid, isophthalic acid and terephthalic acid, sulfonyldibenzoic acid, Diphenylätherdicarbonklare and the isomeric naphthalenedicarboxylic acids are preferably used as dibasic carboxylic acids A5 , as well as dimeric fatty acids by catalyzed dimerization of unsaturated fatty acids (eg tall oil fatty acid) as a mixture of acyclic and be obtained cyclic dicarboxylic acids.
  • unsaturated fatty acids eg tall oil fatty acid
  • Mono- or polyunsaturated aliphatic dicarboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid and mesaconic acid or sorbic acid can also be used. Particular preference is given to adipic acid, maleic acid and the isomeric phthalic acids, in each case individually or in a mixture.
  • Suitable hydroxycarboxylic acids A6 are lactic acid, dimethylolpropionic acid, tartaric acid, grape acid, glycolic acid, dihydroxysuccinic acid and malic acid. This component may also contain mixtures of several of the suitable substances.
  • the polyesters are obtained in known manner by polycondensation of the starting materials A4 to A6 or their ester-forming derivatives (such as methyl esters or halides or anhydrides of the acids or acetates of the alcohols) in bulk or in solution.
  • ester-forming derivatives such as methyl esters or halides or anhydrides of the acids or acetates of the alcohols
  • the known transesterification catalysts can be used.
  • the dimerized and oligomerized unsaturated aliphatic carboxylic acids which are likewise suitable as component A are obtained by di- or oligomerization of mono- or polyunsaturated fatty acids having 6 to 30 carbon atoms. Preference is given to the mixtures of linear branched and cyclic di- and trimers of unsaturated fatty acids with 16 to 24, especially also with 18 carbon atoms, obtained by catalysis with metal oxides.
  • aldehyde and ketone resins obtainable by condensation of Ketones, ketones together with aldehydes, ketones with urea or aldehydes with Urea, having a hydroxyl number of 20 to 300 mg / g, a softening point of 60 to 140 ° C and a number average molar mass of 500 to 3000 g / mol.
  • These resins will be Usually prepared by alkali-catalyzed condensation. suitable Manufacturing processes are described in DRP 337 993, DRP 357 091, DRP 511 092, DE 0 749 836, US Pat. DRP 339 107 and DE-A 28 31 613.
  • Suitable ketone resins are derived from cycloaliphatic ketones such as cyclohexanone or its derivatives such as methylcyclohexanone and tert-butyl cyclohexanone.
  • the resins can be made from these ketones or mixtures thereof obtained by the known methods.
  • Other suitable resins are by condensation of ketones in the presence of urea, substituted ureas or their derivatives such as z.
  • B. 2-imidazolidinone Also suitable are condensation products of ketones and Aldehydes, preferably cycloaliphatic ketones and formaldehyde or its oligomers, also optional in the presence of urea or its derivatives.
  • the resins AB according to the invention are obtainable by reacting the components A and B at elevated temperature, preferably at 100 to 220 ° C., preferably in the melt without addition of a solvent, although optionally under the reaction conditions inert solvent in mass fractions of up to 20% , based on the sum of the masses of components A and B and of the solvent, can be added.
  • the reaction is carried out until the acid number of the condensation product from A and B has reached a value of 25 to 160 mg / g.
  • small amounts of water are formed, which escape at the reaction temperature. It is also preferable to remove the water by azeotropic distillation by using a solvent which is immiscible with water and forms an azeotrope with water.
  • the resins AB thus prepared, optionally after addition of small amounts of a water-dilutable Lösunsgstoffs, neutralized with aqueous alkalis, preferably ammonia solutions or amines.
  • aqueous alkalis preferably ammonia solutions or amines.
  • the amount of alkalis is chosen so that at least half of the acid groups of the resin is neutralized. However, it is preferred to neutralize completely.
  • the mixture is then further diluted to a solids content by mass of preferably from 20 to 60%, particularly preferably from 30 to 50%, by adding water. It is also possible to adjust the concentration of the neutralizing agent so that dilution and neutralization are carried out simultaneously. This gives an aqueous solution or dispersion of the neutralized resin.
  • the resins AB prepared according to the invention are water-dilutable after neutralization. They can be used, for example, for the production of water-dilutable coating compositions. They are excellently suitable as paste resins for the production of low-solvent and solvent-free pigment pastes. They have a high pigment binding capacity, are stable in storage and do not change their viscosity during storage either in the pigment pastes produced therefrom or not at all. These pigment pastes can be easily incorporated into aqueous binders. Compared to directly pigmented paints there is no negative influence on the paint properties.
  • ⁇ is the viscosity of the solution studied and ⁇ s is the viscosity of the pure solvent.
  • the unit commonly used for J is dl / g.
  • copolymers were prepared in a known manner by solution polymerization in isopropanol prepared according to a calculated mass fraction of solids of 50%.
  • the proportions and key figures are summarized in Table 1.
  • the components (A) and (B) were filled in the proportions shown in Table 2 in a suitable reaction vessel.
  • the batch was gradually brought to a circulation temperature of 200 ° C. with stirring and held at this temperature until the indicated acid number was reached.
  • the batch was adjusted with ethylene glycol monobutyl ether to a solids content of 87% and emulsified at 50 ° C with a dilute aqueous ammonia solution.
  • the amount of ammonia and water was chosen to result in a pH of the emulsion of 8.2 to 8.4 and a solids content of 40%.
  • the resin solutions were milky to transparent liquids.
  • Tlen a dimer fatty acid having an average of 36 carbon atoms and an acid number of about 190 mg / g (®Pripol 1017 Unichema) and 50 Tlen a resin of aliphatic aldehydes and urea having a softening temperature of 80 to 90 ° C and a Acid value of about 1.5 mg / g (®Laropal A 81) is prepared by condensation a paste resin PH10 having an acid number of 70 mg / g.
  • the respective amounts of the respective pigments were dispersed in the following pigment paste solution on the bead mill and then subjected to a test of their storability.
  • 250 Tle pigment paste resin, 40% in water 20 Tle Additol® VXW 6213 (wetting agent) 2 Tle Additol® VXW 6210 (Defoamer) 3 Tle Additol® XL 297 (Anti-skinning agent for air-drying paint binders) 100 Tle of water 375 Tle pigment paste preparation pigment
  • Pigment paste resin Tle pigment to 100 parts PH Viscosity in mPa ⁇ s Bearing test P1 ® Hostaperm yellow H4G PH1 175 1188 iO P2 ® Novoperm yellow H10GL PH2 125 470 iO P3 ® Novopermorange HL70 PH7 275 707 iO P4 ® Permanent orange RL70 PH3 200 1102 iO P5 ® Hostaperm pink E
  • the paste resins produced according to the invention are stable on storage and have a high pigment binding capacity.
  • test plates based on the stoving type (AX 246) became 10 minutes after application dried, dried at 80 ° C for 10 minutes and then baked at 130 ° C for 20 minutes. A Hour after firing, the tests were carried out.
  • Paste resins to produce a number of different low-solvent pigment pastes and with Excellent result to pigment paints, without the technical application Property profile of the paints negative influence.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Paints Or Removers (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Extrusion Moulding Of Plastics Or The Like (AREA)
  • Reinforced Plastic Materials (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Lubricants (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
EP98118725A 1997-10-06 1998-10-02 Wasserverdünnbare Harze, Verfahren zu ihrer Herstellung und ihre Verwendung Expired - Lifetime EP0908486B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT98118725T ATE263798T1 (de) 1997-10-06 1998-10-02 Wasserverdünnbare harze, verfahren zu ihrer herstellung und ihre verwendung

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AT1682/97 1997-10-06
AT0168297A AT407253B (de) 1997-10-06 1997-10-06 Wasserverdünnbare harze, verfahren zu ihrer herstellung und ihre verwendung
AT168297 1997-10-06

Publications (3)

Publication Number Publication Date
EP0908486A2 EP0908486A2 (de) 1999-04-14
EP0908486A3 EP0908486A3 (de) 2000-05-24
EP0908486B1 true EP0908486B1 (de) 2004-04-07

Family

ID=3518719

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98118725A Expired - Lifetime EP0908486B1 (de) 1997-10-06 1998-10-02 Wasserverdünnbare Harze, Verfahren zu ihrer Herstellung und ihre Verwendung

Country Status (7)

Country Link
US (1) US6114434A (da)
EP (1) EP0908486B1 (da)
JP (1) JP4870250B2 (da)
AT (2) AT407253B (da)
DE (1) DE59811140D1 (da)
DK (1) DK0908486T3 (da)
ES (1) ES2218741T3 (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2367898A1 (en) * 2002-01-16 2003-07-16 3M Innovative Properties Company Process for preparing improved abrasive article
AT412474B (de) * 2003-07-23 2005-03-25 Surface Specialties Austria Verwendung von wasserverdünnbaren kondensationsharzen als dispergiermittel für wasserverdünnbare pigmentkonzentrate
DE102005010947A1 (de) * 2005-03-10 2006-09-14 Degussa Ag Wässrige Beschichtungsstoffzusammensetzungen mit verbessertem Steinschlagschutz
DE102005010963A1 (de) * 2005-03-10 2006-09-14 Degussa Ag Wässrige Beschichtungsstoffzusammensetzungen für flexible Untergründe
US8575242B2 (en) * 2006-01-16 2013-11-05 Ppg Industries Ohio, Inc. Coating of organic and inorganic pigments with acrylic resins
CN102070978B (zh) * 2010-12-14 2012-07-04 惠州市长润发涂料有限公司 一种乐器专用清面漆及其制备方法
EP2754704A1 (en) * 2013-01-09 2014-07-16 ALLNEX AUSTRIA GmbH Paste resin

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE339107C (de) * 1918-06-01 1921-07-13 Basf Ag Verfahren zur Darstellung von Kunstharz
DE337993C (de) * 1919-06-13 1921-06-10 Basf Ag Verfahren zur Darstellung von harzartigen Produkten
DE357091C (de) * 1919-06-13 1922-08-17 Basf Ag Verfahren zur Darstellung von harzartigen Produkten
DE511092C (de) * 1925-10-21 1930-11-06 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von harzartigen Produkten
DE749836C (de) * 1941-08-21 1944-12-07 Verfahren zur Herstellung von oel- oder harzartigen Kondensationsprodukten aus Cyclohexanon und Aldehyden
BE513957A (da) * 1951-09-08
CH561269A5 (da) * 1970-07-22 1975-04-30 Vianova Kunstharz Ag
JPS5717894B2 (da) * 1972-12-09 1982-04-13
US4123404A (en) * 1975-05-12 1978-10-31 Whittaker Corporation Water-based coatings
JPS5416540A (en) * 1977-07-08 1979-02-07 Kansai Paint Co Ltd Thermosetting aqueous coating composition
DE2831613C2 (de) * 1978-07-19 1982-03-18 Basf Ag, 6700 Ludwigshafen Verfahren zur Herstellung von Polykondensationsprodukten
DE3260393D1 (en) * 1981-04-01 1984-08-23 Vianova Kunstharz Ag Process for the preparation of a binding agent modified by a phenolic resin
DE3406474A1 (de) * 1984-02-23 1985-08-29 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung waessriger keton-harz- oder keton/aldehyd-harz-dispersionen und deren verwendung
JPH0699662B2 (ja) * 1986-12-22 1994-12-07 日本油脂株式会社 水性分散型塗料
AT388921B (de) * 1987-06-17 1989-09-25 Vianova Kunstharz Ag Wasserverduennbare streichlacke auf der basis von wasserloeslichen alkydharzen
AT396244B (de) * 1990-12-27 1993-07-26 Vianova Kunstharz Ag Wasserverduennbare lackbindemittel auf der basis von acrylatcopolymerisaten und deren verwendung
AT397508B (de) * 1990-12-27 1994-04-25 Vianova Kunstharz Ag Wasserverdünnbare lackbindemittel auf der basis von acrylatcopolymerisaten und deren verwendung
DE4404809A1 (de) * 1994-02-16 1995-08-17 Huels Chemische Werke Ag Keton-Aldehydharze mit breiter Verträglichkeit, Verfahren zu ihrer Herstellung und ihre Verwendung

Also Published As

Publication number Publication date
US6114434A (en) 2000-09-05
AT407253B (de) 2001-02-26
ATA168297A (de) 2000-06-15
ES2218741T3 (es) 2004-11-16
EP0908486A2 (de) 1999-04-14
JP4870250B2 (ja) 2012-02-08
JPH11171953A (ja) 1999-06-29
EP0908486A3 (de) 2000-05-24
ATE263798T1 (de) 2004-04-15
DK0908486T3 (da) 2004-08-09
DE59811140D1 (de) 2004-05-13

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